New insight into the reaction of singlet oxygen with sulfur-containing cyclic alkenes: dye-sensitized photooxygenation of 5,6-dihydro-1,4-dithiins

The reaction of 3-methyl-5,6-dihydro-1,4-dithiins with singlet oxygen affords dicarbonyl compounds and/or ring-contracted ketosulfoxides, the latter regio- and stereoselectively, depending on the nature of the substituent at C-2 and on the reaction conditions. In competition with normal fragmentation, the intermediate dioxetanes, derived from [2 + 2] cycloaddition of singlet oxygen to the double bond, undergo an intramolecular oxygen transfer to the sulfur-1 atom, leading to labile epoxide intermediates. The latter convert to cis- and trans-ketosulfoxides through a non-concerted S-4 migration. This pathway is promoted by the electron-withdrawing group at C-2 and, for monosubstituted amide, by the solvent basicity. S-Oxidation of dithiins is insignificant, except for the monosubstituted amide derivative or in the presence of protic species, and occurs selectively at the S-1 atom

Antimicrobial and anti-biofilm properties of novel synthetic lignan-like compounds

Antibiotic resistance and biofilm tolerance are among the principal factors involved in the persistence of chronic infections. The need for new antimicrobials is an ever-increasing challenge in clinical environments and in the control of global health. Arylfurans form a set of structures that have been identified in many natural products, e.g. lignans. Lignans are a sub-group of non-flavonoid polyphenols that play an active role in plants’ defense against bacteria and fungi infections. The aim of this study was to identify novel synthetic arylfurans and lignan-like arylbenzylfurans exhibiting antimicrobial properties. The molecules synthetized were tested against Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus and S. epidermidis. We found that among tested compounds, arylbenzylfuran 11 was active against S. aureus and S. epidermidis with an MIC of 4 μg ml-1. Compound 11 was also active on methicillin-resistant S. aureus and S. epidermidis. By confocal laser scanning microscopy, we showed that 32 μg ml-1 of compound 11 was able to induce a significant reduction in S. aureus and S. epidermidis biofilms viability. Finally, we demonstrated that compound 11 was not cytotoxic on HaCat cells up to 128 μg ml-1. This work shows the antimicrobial and anti-biofilm potential of a synthetic lignan-like furan

Antimicrobial and anti-biofilm properties of novel synthetic lignan-like compounds

Antibiotic resistance and biofilm tolerance are among the principal factors involved in the persistence of chronic infections. The need for new antimicrobials is an ever-increasing challenge in clinical environments and in the control of global health. Arylfurans form a set of structures that have been identified in many natural products, e.g. lignans. Lignans are a sub-group of non-flavonoid polyphenols that play an active role in plants' defense against bacteria and fungi infections. The aim of this study was to identify novel synthetic arylfurans and lignan-like arylbenzylfurans exhibiting antimicrobial properties. The molecules synthetized were tested against Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus and S. epidermidis. We found that among tested compounds, arylbenzylfuran 11 was active against S. aureus and S. epidermidis with an MIC of 4 μg ml-1. Compound 11 was also active on methicillin-resistant S. aureus and S. epidermidis. By confocal laser scanning microscopy, we showed that 32 μg ml-1 of compound 11 was able to induce a significant reduction in S. aureus and S. epidermidis biofilms viability. Finally, we demonstrated that compound 11 was not cytotoxic on HaCat cells up to 128 μg ml-1. This work shows the antimicrobial and anti-biofilm potential of a synthetic lignan-like furan